Savage Love | Savage Love | Chicago Reader

Savage Love 

Sign up for our newsletters Subscribe

My boyfriend of four years enjoys wearing women's clothing and acting like a submissive woman when we have sex. Nothing gets him off more. We have only just started exploring his fetish in the past year because he has been ashamed of it all his life. I have encouraged him so far, and now we have a couple hundred dollars' worth of sexy women's clothing that fits him. Last night he asked me if he could wear a latex mask of a woman's face during sex. That crossed the line for me. I hate it when he puts on skirts and high heels and asks me to fuck him. It's a huge turnoff. I have not enjoyed sex with him for months. I want him to be sexually satisfied, but his fetish disgusts me. I'm a straight woman, and I want to have sex with a man who is acting like a man. What do I do? --Femme Teasing Mask

First, for all the folks reading this who are thinking, "Latex mask of a woman's face?!": Yes, this is a real fetish and no, FTM is not making this up. But don't take my word for it: surf on over to, where you'll find pictures of men engaged in "female masking" and, if you're so inclined, you can purchase a lovely female latex mask of your very own. is run by Kerry, "a straight, male crossdresser who loves to make and wear lycra costumes along with high heels, wigs, and latex masks," according to the bio on his Web site. At first, Kerry made masks only for his own enjoyment; it wasn't until after other cross-dressers started asking him if they could buy his masks that he decided to go into the mask-making business. I contacted Kerry via his Web site, FTM, and asked him if he had any advice for you.

"It's too late to put the genie back in the bottle," Kerry said. "Her boyfriend is not going to quit cross-dressing, and obviously wants to take it further. If she doesn't want a cross-dressing boyfriend, she'll need to get another boyfriend."

I agree with Kerry, FTM. You've created a monster, kiddo, and you need to take some responsibility for the mess you've made. It's one thing to encourage your partner to explore a fetish that you're willing to play along with or, if you're lucky, you enjoy on some level. But encouraging your partner to explore a fetish that disgusts you? That's as good as signing your relationship's death warrant!

While I think you should get yourself another boyfriend, FTM, I want to impress upon you the importance of dumping your current boyfriend without destroying him. For the first time in his life your soon-to-be ex has a healthy attitude toward his pervy desires--and he has you to thank for that. If you dump him now and blame the cross-dressing, all the shame and guilt and self-loathing will rush back in. So don't tell him the real reason why you're leaving. Let him think that it's not the cross-dressing and the latex masks but his breath or his fashion sense or his family or whatever. Leave him, FTM--just leave him with his newfound sense of pleasure in his fetish, OK?

But if you want to stay with this boyfriend and try to make it work, tell your boyfriend how you really feel. Then hand him this column, because Kerry's got some advice for him:

"To him, the boyfriend, I would say that he shouldn't make his girlfriend participate in sexual activities she has no interest in," Kerry said. "I would tell him to dress up and mask on the side and when it's time for sex, use your imagination. My wife knew about my cross-dressing and female masking before we got married. I love to mask and go out to nightclubs, Halloween events, and science-fiction conventions. It really turns me on. But it doesn't do anything for my wife, who I'm sure would be in much the same boat as the woman who wrote you if I insisted on doing sex in high drag. So I don't. Like I said, I let my imagination do the work for me, and my wife gets 'a man acting like a man' in bed. Everybody is happy."

Finally, to the folks who, like FTM, are creeped out by the idea of female masking, Kerry would like to say this: "I get comments from people from time to time in public about my masks, typically along the lines of 'You're really creeping me out.' Even among cross-dressers I'm considered a bit weird. A lot of people find masks very unsettling, particularly the fixed, unmoving eyes and expressionless faces. It's only natural and I don't let it bug me, but neither am I in their face about showing more tolerance. But certainly, in the privacy of my own house, I'm not doing anyone any harm. It's just a fetish."

Amen, sister.

I am a 21-year-old gay male and I finally met a man I'm interested in. The problem is this: I'm not sure about him. Occasionally he mentions a girlfriend. I can't see how this is so. His gestures, actions, and mannerisms around me suggest that he is not hetero. Here's my Top Ten List of Suspicious Behaviors I've Witnessed:

1.) He attempted to feel the texture of my boxer shorts (while I was wearing them!).

2.) The time he told me I had beautiful eyes.

3.) Knee tickling.

4.) Intentional leg touching under tables while out dining.

5.) His conversations with mutual friends regarding my sexuality.

6.) Comments about "life partners" instead of wives, etc.

7.) Complaining about "girlfriend" never wanting to have sex.

8.) Saying things I do are "cute."

9.) Opens doors for me.

10.) Homolike attire. Not metrolike attire.

I know this may sound a little neurotic, but I could use some advice, as the mystery of the relationship is making me frustrated.

--Sexually Frustrated

1.) Straight guys don't care about the texture of boxer shorts--their own or anyone else's.

2.) Straight guys don't compliment other guys on their beautiful eyes.

3.) Please.

4.) OK, that's enough.

Look, this guy wants to smoke your pole, SF, but this pole smoker is a chickenshit--excuse me, he's "questioning," i.e., he hasn't worked up the nerve to come out to himself, his friends, family, and imaginary girlfriend yet. Still, he's clearly desperate for dick, he's attracted to you, and he wants you to jump him--hence the groping, tickling, compliments, leading comments about being horny, and on and on. This is standard closet-case stuff. So if he's dying for it, SF, and he knows you're gay, and he knows you'll be thrilled, why doesn't he make a move? Because then he would have to admit to himself that he's gay. But if you jump him, SF, he'll be able to blame you for all the pole smoking that ensues. "I'm straight," he'll tell himself. "I was seduced! I'm innocent!"

The question you face, SF, is not whether or not this guy is gay. He's gay. The question is whether you want to get involved with someone who is going to blame you for every blow job he gives you. It's fun for the first, oh, dozen or so, but being a closet case's boyfriend gets pretty tiresome pretty quick.


Subscribe to this thread:

Add a comment

More by Dan Savage

  • Listen up, guys

    Listen up, guys

    Advice for would-be allies, ethical affair partners, and successful daters
    • Nov 6, 2019
  • Quick hits

    Quick hits

    Dan Savage advises a dude held back by his small dick, a teacher who wants to moonlight as a sex worker, and more.
    • Oct 30, 2019
  • School for sexual scoundrels

    School for sexual scoundrels

    How can inveterate cheaters find happiness? Facing up to facts is a start.
    • Oct 23, 2019
  • More »

Agenda Teaser

November 12
Performing Arts
Broken Bone Bathtub Humboldt Park
October 30

Tabbed Event Search

Popular Stories